Tert-butyl 2-ethynyl-6-methoxyphenylcarbamate → Tert-butyl 2-methoxy-6-(3-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-3-oxoprop-1-ynyl)phenylcarbamate

To tert-butyl 2-ethynyl-6-methoxyphenylcarbamate (1.77 g, 7.18 mmol) in THF (40 mL) was added butyllithium (0.919 g, 14.4 mmol) at −78° C., and the reaction was stirred for 1 hour. N-methoxy-7-(2-methoxyethoxy)-N-methylimidazo[1,2-a]pyridine-3-carboxamide (1.67 g, 5.98 mmol) in THF (55 mL) was then added to the reaction mixture dropwise. After the addition, the cold bath was removed and the reaction was warmed to ambient temperature. Following a 2 hour stir at ambient temperature, the reaction mixture was poured into cold saturated NH4Cl (40 mL) and EtOAc (50 mL). The phases were separated and the aqueous phase was extracted with EtOAc, dried over Na2SO4, filtered and concentrated. The residue was triturated with DCM to give product as a solid. The DCM solution was concentrated and purified by flash column chromatography (EtOAc/MeOH 10:0 to 10:1) to provide the desired product.

1. additionAfter the addition
2. customthe cold bath was removed
3. waitFollowing a 2 hour
4. stirringstir at ambient temperature
5. additionthe reaction mixture was poured into cold saturated NH4Cl (40 mL) and EtOAc (50 mL)
6. customThe phases were separated
7. extractionthe aqueous phase was extracted with EtOAc
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was triturated with DCM
12. customto give product as a solid
13. concentrationThe DCM solution was concentrated
14. custompurified by flash column chromatography (EtOAc/MeOH 10:0 to 10:1)

ORDレコード

ord-e18b4719a2b54b2cb3312e7889dcd2db

出典データセット

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08138181B2